N,N'-(p-xylylene)di(2-methyl)alamine acid | 1395498-86-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N,N'-(p-xylylene)di(2-methyl)alamine acid
• 英文别名: H2PDIMALa；2-[[4-[(2-Carboxypropan-2-ylamino)methyl]phenyl]methylamino]-2-methylpropanoic acid
• CAS: 1395498-86-8
• 化学式: C₁₆H₂₄N₂O₄
• 分子量: 308.378
• InChiKey: QVKOCZJUFOQUQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.5
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  98.7
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  甲醇 、 二吡啶并[3,2-a:2',3'-c]吩嗪 、 copper(II) perchlorate hexahydrate 、 N,N'-(p-xylylene)di(2-methyl)alamine acid 、 水 在 LiOH 作用下， 以 甲醇 、 水 为溶剂， 以66%的产率得到[Cu2(dppz)2(PDIMALa)(H2O)2][ClO4]2*MeOH
  参考文献：
  名称：

  Synthesis, crystal structure, DNA-binding properties, cytotoxic and antioxidation activities of several ternary copper(II) complexes with a new reduced Schiff base ligand

  摘要：

  Three new ternary copper(II) complexes, [Cu-2(phen)(2)(PDIMAla)(H2O)(2)](ClO4)(2)center dot CH3OH (1), [Cu-2(dpq)(2) (PDIMAla)(H2O)(2)](ClO4)(2)center dot CH3OH (2) and [Cu-2(dppq)(2)(PDIMAla)(H2O)(2)](ClO4)(2)center dot CH3OH (3) (phen = 1,10-phenanthroline, dpq = dipyrido[3,2:2',3'-f]quinoxaline, dppz = dipyrido[3,2-a:2',3'-c]phenazine, H2PDI-MAla = N,N'-(p-xylylene)di-alanine acid) have been synthesized and the complex 1 has been structurally characterized by single-crystal X-ray crystallography, spectrometric titrations, ethidium bromide displacement experiments, CD (circular dichroism) spectral analysis and viscosity measurements. The results indicate that the three compounds, especially the complex 3, can strongly bind to calf-thymus DNA (CT-DNA). The intrinsic binding constants K-b of the ternary copper(II) complexes with CT-DNA are 0.38 x 10(5), 1.4 x 10(5) and 7.8 x 10(5) for 1, 2 and 3, respectively. Comparative cytotoxic activities of the copper(II) complexes are also determined by acid phosphatase assay. The results show that the ternary copper(II) complexes have significant cytotoxic activity against the human hepatic (HepG2), human promyelocytic leukemia (HL60) and human prostate (PC3) cell lines. Investigation of antioxidation property show that all the copper(II) complexes have strong scavenging effects for hydroxyl radicals. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.05.014
• 作为产物：
  描述：

  在 sodium tetrahydroborate 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以1.37 g的产率得到N,N'-(p-xylylene)di(2-methyl)alamine acid
  参考文献：
  名称：

  Synthesis, crystal structure, DNA-binding properties, cytotoxic and antioxidation activities of several ternary copper(II) complexes with a new reduced Schiff base ligand

  摘要：

  Three new ternary copper(II) complexes, [Cu-2(phen)(2)(PDIMAla)(H2O)(2)](ClO4)(2)center dot CH3OH (1), [Cu-2(dpq)(2) (PDIMAla)(H2O)(2)](ClO4)(2)center dot CH3OH (2) and [Cu-2(dppq)(2)(PDIMAla)(H2O)(2)](ClO4)(2)center dot CH3OH (3) (phen = 1,10-phenanthroline, dpq = dipyrido[3,2:2',3'-f]quinoxaline, dppz = dipyrido[3,2-a:2',3'-c]phenazine, H2PDI-MAla = N,N'-(p-xylylene)di-alanine acid) have been synthesized and the complex 1 has been structurally characterized by single-crystal X-ray crystallography, spectrometric titrations, ethidium bromide displacement experiments, CD (circular dichroism) spectral analysis and viscosity measurements. The results indicate that the three compounds, especially the complex 3, can strongly bind to calf-thymus DNA (CT-DNA). The intrinsic binding constants K-b of the ternary copper(II) complexes with CT-DNA are 0.38 x 10(5), 1.4 x 10(5) and 7.8 x 10(5) for 1, 2 and 3, respectively. Comparative cytotoxic activities of the copper(II) complexes are also determined by acid phosphatase assay. The results show that the ternary copper(II) complexes have significant cytotoxic activity against the human hepatic (HepG2), human promyelocytic leukemia (HL60) and human prostate (PC3) cell lines. Investigation of antioxidation property show that all the copper(II) complexes have strong scavenging effects for hydroxyl radicals. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.05.014